Regrettable Star Trek Moments (Original Cast Only)

In case you've spent the last six months in the Vault of Tomorrow with a crate of Romulan ale, there's a new Star Trek movie coming out. And after 20-odd years of dealing with the Enterprise-D and dry Next Generation-style shenanigans, it's nice to see the old crew, even if it is in name only.

This isn't to say the original cast has nothing to be embarrassed about. If anything, it was almost impossible to whittle the list down to just five.

5. "Way to Eden" -- TOS Season 3 (1969)

The only things worse than hippies are space hippies. And there's not much funnier than watching perpetual movie tough guy Charles Napier wearing a miniskirt and strumming a space lute. He would later make up for it by portraying "General Denning" on Deep Space Nine.

Widely, and correctly, regarded as the best Trek film, Wrath nonetheless suffers from this widely parodied scene, which is perhaps the purest example of Shatner's particular talents.

3. "Let That Be Your Last Battlefield" -- TOS Season 3 (1969)

You doubt the prejudice-ending advice dispensed by a man who kissed a black woman? No wonder your world destroyed itself.

2. The Flying Vulcan -- Star Trek V: The Final Frontier (1989)

The last few original cast Trek movies started feeling a lot like latter era Roger Moore Bond flicks, what with a couple of near-60 year olds bouncing around the universe with an almost gleeful disregard for their own ridiculousness. This scene captures all of that in a scant 20 seconds.

1. The Death of Kirk -- Star Trek Generations (1994)

Producer Rick Berman never exhibited any particular love for the original series, so giving Kirk such an ignominious demise (falling off a cliff) instead of having him snuff it at the helm of the Enterprise, flying it kamikaze-style into the Klingon homeworld while simultaneously banging an Orion slave girl and Yeoman Rand, is hardly surprising. It's still inexcusable, however.